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Williams, 40, and Federer, 41, have both announced in short succession their plans to retire, leaving the tennis world without two of its most iconic players.
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Several of the players marked firsts for the sport's history, while for Serena Williams, the tournament may have been her last match.
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The 23-time Grand Slam champion staved off five match points to prolong the three-hours-plus proceedings, but could not do more, and was eliminated from the U.S. Open in the third round.
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Serena Williams says she is close to retirement. We take a look at her life and career from Compton to Wimbledon, and the impact she has had on athletes, particularly African American women.
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Serena Williams eliminated No. 2 seed Anett Kontaveit at the U.S. Open to ensure that she will play at least one more singles match at what she's hinted will be the last tournament of her career.
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When the tennis megastar announced her plans to retire from competition last week, she said her future will involve a renewed focus on a venture capital firm she quietly founded eight years ago.
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Williams, a 23-time grand slam champion, dominated the sport for decades.
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"I'm turning 41 this month, and something's got to give," Williams told Vogue. She attributed the choice to the competing urges of wanting another child while facing off with the world's best players.
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Williams' announcement marks her return to professional competition since sustaining an injury at the tournament last year. It's also another chance for her to win her 24th Grand Slam singles title.
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"We don't condone anyone hitting anyone else unless it's in self-defense," the father of Venus and Serena Williams told NBC News. Smith won an Oscar for portraying Williams in the movie King Richard.